Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 6, Pages 1871-1882Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.200902548
Keywords
glycosylation; gold; homogeneous catalysis; sialylation; triterpene saponin
Categories
Funding
- National Natural Science Foundation of China [20932009, 20621062]
- Ministry of Sciences and Technology of China [2009ZX09311-001]
Ask authors/readers for more resources
Glycosyl ortho-alkynylbenzoates have emerged as a new generation of donors for glycosidation under the catalysis of gold(I) complexes such as Ph(3)PAuOTf and Ph(3)PAuNTf(2) (Tf= trifluoromethanesulfonate). A wide variety of these donors, including 2-deoxy sugar and sialyl donors, are easily prepared and shelf stable. The glycosidic coupling yields with alcohols are generally excellent; even direct coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent alpha-selective glycosylation with a 2-deoxy sugar donor and beta-selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective glycosylation of the carboxylic acid and a new one-pot sequential glycosylation sequence have been implemented.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available